Structural Characterisation of 1,3-Dioxolium Compounds 6 5 ...

Supplementary Information for:

B(C6F5)3 Promoted Cyclisation of Internal Propargyl Esters: Structural Characterisation of 1,3-Dioxolium CompoundsRebecca L. Melen,a¥ Max M. Hansmann,b¥ Frank Rominger,b A. Stephen K. Hashmi*b,c and Douglas W. Stephan*a,c

aDepartment of Chemistry, University of Toronto, 80 St. George Street,Toronto, Ontario, M5S 3H6, Canada

bOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

cChemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah 21589, Saudi Arabia.

General procedures

With the exception of the synthesis of starting materials, all reactions and manipulations were carried out under an atmosphere of dry, O2-free nitrogen using standard double-manifold techniques with a rotary oil pump. An argon-filled glove box (MBRAUN) was used to manipulate solids including the storage of starting materials, room temperature reactions, product recovery and sample preparation for analysis. Molecular sieves (4 Å) were dried at 120ºC for 24 h prior to use. All solvents (toluene, CH2Cl2, pentane) were dried by employing a Grubbs-type column system (Innovative Technology) or a solvent purification system MB SPS-800, degassed and stored over molecular sieves under a nitrogen atmosphere. Deuterated solvents were dried over molecular sieves before use. Chemicals were purchased from commercial suppliers and used as received. B(C6F5)3 was prepared based on a slightly modified synthesis reported in the literature.1 1H, 13C, 11B and 19F NMR spectra were recorded on a Bruker Avance III, Bruker Avance 400, Varian Unity 500, Bruker Avance-III-300, Bruker Avance DRX-300, Bruker Avance 500 or Bruker Avance 600. Chemical shifts are expressed as parts per million (ppm, δ) downfield of tetramethylsilane (TMS) and are referenced to CDCl3 (7.26 / 77.16 ppm) and CD2Cl2 (5.32 / 53.80 ppm) as internal standards. NMR spectra were referenced to CFCl3 (19F) or 1,2-difluorobenzene (-139 ppm) and BF3·Et2O/CDCl3 (11B). The description of signals include: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet and br. = broad. All coupling constants are absolute values and J values are expressed in Hertz (Hz). All spectra were analyzed assuming a first order approximation. A Perkin-Elmer Analyzer was used for carbon, hydrogen and nitrogen elemental analyzes. High resolution mass spectrometry was performed in house employing DART or electrospray ionization techniques in positive ion mode. Mass spectral data were recorded on an AB/Sciex QStarXL mass spectrometer (ESI), a JEOL AccuTOF model JMS-T1000LC mass spectrometer and an ICR Apex-Qe (DART). Mass spectral data collected in the chemistry department of the University Heidelberg (MS and HRMS) were collected using a Bruker ApexQe FT-ICR-MS spectrometer under the direction of Dr. J. Gross.

1. Experimental Details

General procedure A:

Electronic Supplementary Material (ESI) for ChemComm.This journal is © The Royal Society of Chemistry 2014

Triethylamine (1.0 equiv.) and DMAP (5 mol%) were added to a solution of the propargyl alcohol

(1.0 equiv.) in CH2Cl2 and was stirred for 15 min. The solution was then cooled to 0°C and the acyl

chloride was added dropwise. The resulting mixture was stirred at this temperature for 30 min and was

allowed to warm to room temperature and further stirred. After quenching the reaction with water the

aqueous layer was extracted with CH2Cl2 (x2). The collective organic phases were washed with brine,

dried with MgSO4, filtered, and the solvent was removed under vacuum and the product purified by

column chromatography on SiO2.

But-2-yn-1-yl 4-methylbenzoate (1)

O

O

Me Me

According to general procedure A, 2-butyne-1-ol (374 µl, 5.0 mmol), DMAP (12.2 mg), NEt3 (693 µl,

8.0 mmol) and p-toluoyl chloride (661 µl, 5.0 mmol) were reacted in 15 ml CH2Cl2. Column

chromatography on SiO2 (hexane/EtOAc, 19:1) afforded the product as a colourless liquid (788 mg,

4.19 mmol, 84%).

Rf = 0.32 (petrolether/EtOAc, 19:1).

IR (thin film) νmax = 3036 cm-1, 2945, 2921, 2320, 2241, 1732, 1613, 1578, 1509, 1438, 1409, 1374, 1310, 1281, 1255, 1209, 1178, 1154, 1110, 952, 841.

1H NMR (400 MHz, CDCl3, 298 K): 7.96 (d, 3JHH = 8.2 Hz, 2H), 7.24 (d, 3JHH = 8.2 Hz, 2H), 4.87 (q, 5JHH = 2.4 Hz, 2H, -CH2), 2.41 (s, 3H, -CH3), 1.88 (t, 4JHH = 2.4 Hz, 3H, -C≡C-Me).

13C{1H} NMR (100 MHz, CDCl3, 298 K): 166.2 (s), 144.0 (s), 130.0 (s), 129.2 (s), 127.2 (s), 83.3 (s), 73.5 (s), 53.3 (s), 21.8 (s), 3.9 (s).

EA (elemental analysis) calcd (%) for C12H12O2: C 76.57, H 6.41%; Obs. C 75.53, H 6.70%.

EI (+) (m/z): 188.1 [M]+ (74), 143.1 (8), 129.1 (15), 120.1 (15), 119.0 (100) 91.1 (22).

HRMS-EI (+) (m/z): calcd for C12H12O2,188.0837; found, 188.0834.

Hex-2-yn-1-yl 4-methylbenzoate (2)

O

O

Me Me

According to general procedure A, 2-hexyne-1-ol (2.2 ml, 20.4 mmol), DMAP (45.0 mg), NEt3

(2.82 ml, 20.4 mmol) and p-toluoyl chloride (2.69 ml, 20.4 mmol) were reacted in 40 ml CH2Cl2.

Column chromatography on SiO2 (petroleum ether /EtOAc, 20:1) afforded the product as a colourless

liquid (3.06 g, 14.1 mmol, 69%).

Rf = 0.26 (petroleum ether /EtOAc, 50:1).

IR (thin film) νmax = 3036 cm-1, 2964, 2873, 2307, 2239, 1730, 1613, 1577, 1509, 1454, 1436, 1409, 1372, 1339, 1310, 1276, 1209, 1178, 1150, 1104, 1021, 952, 894.

1H NMR (400 MHz, CDCl3, 298 K): 8.00 (d, 3JHH = 8.3 Hz, 2H), 7.23 (d, 3JHH = 8.3 Hz, 2H), 4.90 (t, 5JHH = 2.2 Hz, 2H), 2.41 (s, 3H), 2.22 (tt, 3JHH = 7.1 Hz, 5JHH = 2.2 Hz, 2H), 1.55 (tq, 3JHH = 7.3 Hz, 7.1 Hz, 2H), 0.99 (t, 3JHH = 7.3 Hz, 3H).

13C{1H} NMR (100 MHz, CDCl3, 298 K): 166.2 (s), 143.9 (s), 130.0 (s), 129.2 (s), 127.3 (s), 87.6 (s), 74.5 (s), 53.3 (s), 22.0 (s), 21.8 (s), 20.9 (s), 13.6 (s).

EI (+) (m/z): 216.1 [M]+ (11), 188.1 (24), 187.1 (24), 162.0 (7), 137.1 (8), 120.0 (43), 119.0 (100), 91.1 (54), 79.1 (28).

HRMS-EI (+) (m/z): calcd for C14H16O2, 216.1150; found, 216.1139.

Hex-2-yn-1-yl pivalate (3)

O

O

Me

According to general procedure A, 2-hexyne-1-ol (2.0 ml, 18.2 mmol), DMAP (110 mg), NEt3 (2.52

ml, 18.2 mmol) and pivaloyl chloride (2.24 ml, 18.2 mmol) were reacted in 50 ml CH2Cl2. Column

chromatography on SiO2 (petroleum ether /EtOAc, 25:1) afforded the product as a colourless liquid

(2.79 g, 15.3 mmol, 84%).

Rf = 0.40 ( petroleum ether /EtOAc, 25:1)

IR (thin film) νmax = 2967 cm-1, 2937, 2909, 2874, 2306, 2239, 1739, 1537, 1480, 1460, 1397, 1366, 1339, 1280, 1229, 1156, 1033, 964, 941, 914.

1H NMR (400 MHz, CDCl3, 298 K): 4.64 (t, 5JHH = 2.3 Hz, 2H), 2.18 (tt, 3JHH = 7.1 Hz, 5JHH = 2.2 Hz, 2H), 1.53 (tq, 3JHH = 7.4 Hz, 7.1 Hz, 2H), 1.21 (s, 9H), 0.97 (t, 3JHH = 7.4 Hz, 3H).

13C{1H} NMR (100 MHz, CDCl3, 298 K): 178.0 (s), 87.2 (s), 74.6 (s), 52.9 (s), 38.9 (s), 27.2 (s, 3C), 22.0 (s), 20.9 (s), 13.5 (s).

EI (+) (m/z): 182.1 [M]+ (4), 154.1 (12), 153.1 (19), 126.1 (21), 98.1 (7), 85.1 (24), 81.1 (11), 79.1 (29), 70.0 (10).

HRMS-EI (+) (m/z): calcd for C11H18O2, 182.1307; found, 182.1300.

Synthesis of (4)

O

Op-tol

Me

B(C6F5)3

B(C6F5)3 (205 mg, 0.4 mmol) was dissolved in toluene (3 ml) and was added to but-2-yn-1-yl 4-

methylbenzoate (75 mg, 0.4 mmol). The reaction was left to stand at room temperature for 4 days

affording a purple solution and colourless crystals of the product. The remaining solution was

decanted off and the remaining solid washed with pentane (3 x 2 ml) and dried in vacuo to give the

pure product (114 mg, 41%, 0.16 mmol).

1H NMR (500 MHz, CD2Cl2, 298K): 7.86 (d, 3JHH = 8.67 Hz, 2H, Ar-H), 7.52 (m, 2H, Ar-H), 2.95 (m, br., 2H, -CH2), 2.55 (s, 3H, -CH3), 2.20 (s, 3H, CH3).

11B NMR (128 MHz, CD2Cl2, 298 K): -14.3 (s).

19F NMR (377 MHz, CD2Cl2, 298 K): -132.8 (d, 2F, JFF = 22.6 Hz, o-F), -161.9 (t, 1F, JFF = 20.4 Hz, p-F), -166.2 (m, 2F, m-F).

13C{1H} NMR (125 MHz, CD2Cl2, 298K): 173.0 (s, dioxolium), 157.1 (s, dioxolium), 153.8 (s), 148.7 (m, 1JCF = 242 Hz), 143.5 (s, dioxolium), 139.0 (m, 1JCF ca. 234 Hz), 137.2 (m, 1JCF ca. 246 Hz), 132.42 (s), 131.0 (s), 113.7 (s), 23.1 (s), 18.9 (m), 9.0 (s), the signals due to the carbon atoms bonded to boron in the C6F5 rings could not be observed.

EA (elemental analysis) calcd (%) for C30H12O2BF15: C 51.46; H 1.73; Found: C 51.33, H 1.94.

EI+ MS, m/z: 700.1 (calcd for [M]+: 700.1), 533.0 (calcd for [(M-C6F5)]+: 533.0), 119.0 (calcd for [p-tol-≡O]+: 119.0).

Synthesis of (5)

O

Op-tol

B(C6F5)3

Me

Hex-2-yn-1-yl 4-methylbenzoate (169 mg, 0.78 mmol) was added to a solution of B(C6F5)3 (400 mg, 0.78 mmol) dissolved in CH2Cl2 (4 ml). The solution was stirred at room temperature for 2 days. Slow vapour diffusion of pentane into the solution at -20°C afforded yellow crystals of the product. The remaining solution was decanted off and the remaining solid washed with pentane (3 x 2 ml) and dried in vacuo to give the pure product (480 mg, 85%, 0.66 mmol).

IR (thin film) νmax = 1691 cm-1, 1640, 1602, 1540, 1511, 1441, 1382, 1361, 1304, 1274, 1255, 1213, 1189, 1129, 1078, 970, 958, 909, 829, 803, 768, 742, 703, 658.

1H NMR (500 MHz, CD2Cl2, 298K): 7.85 (d, 3JHH = 8.4 Hz, 2H, Ar-H), 7.52 (d, 3JHH = 8.4 Hz, 2H, Ar-H), 2.97 (m, br., 2H, -CH2-BR3), 2.54 (s, 3H), 2.50 (t, 3JHH = 7.4 Hz, 2H), 1.58 (tq, 3JHH = 7.4 Hz, 7.4 Hz, 2H), 0.95 (t, 3JHH = 7.4 Hz, 3H).

11B NMR (160 MHz, CD2Cl2, 298 K): -14.4 (s).


13C{1H} NMR/ 13C{1H,19F} NMR (125 MHz, CD2Cl2, 298K): 173.1 (s, dioxolium), 156.9 (s, dioxolium), 153.7 (s), 148.8 (m, 1JCF = 239 Hz), 147.2 (s, dioxolium), 139.0 (m, 1JCF ca. 234 Hz), 137.2 (m, 1JCF ca. 246 Hz), 132.2 (s), 131.0 (s), 124.4 (q, 1JCB = 48.5 Hz), 113.2 (s), 25.3 (s), 23.1 (s), 21.0 (s), 18.9 (q, 1JCB = 39.0 Hz), 13.6 (s).

EA (elemental analysis) calcd (%) for [C32H16BF15O2*0,5CH2Cl2]: C 50.65; H 2.22; Found: C 50.47, H 2.49.

HRFAB (+) (m/z): calcd for C32H16O2BF15, 728.1004; found, 728.1041.

Synthesis of (6)

O

O

B(C6F5)3

Me

Hex-2-yn-1-yl pivalate (107 mg, 0.59 mmol) was added to a solution of B(C6F5)3 (300 mg, 0.59 mmol)

dissolved in toluene (2 ml). The solution was stirred at room temperature for 2 days. Slow vapour

diffusion of pentane into the solution at -20°C afforded colorless crystals of the product. The

remaining solution was decanted off and the remaining solid washed with pentane (3 x 2 ml) and dried

in vacuo to give the pure product (320 mg, 78%, 0.46 mmol).

IR (thin film) νmax = 1687 cm-1, 1643, 1559, 1514, 1498, 1457, 1378, 1273, 1247, 1220, 1203, 1086, 978, 963, 920, 903, 812, 802, 779, 767, 736, 698, 669, 648.

1H NMR (500 MHz, CD2Cl2, 298K): 2.90 (m, br., 2H, -CH2-BR3), 2.38 (t, 3JHH = 7.7 Hz, 2H), 1.48 (tq, 3JHH = 7.7 Hz, 7.5 Hz, 2H), 1.40 (s, 9H), 0.90 (t, 3JHH = 7.5 Hz, 3H).

11B NMR (160 MHz, CD2Cl2, 298 K): -14.4 (s).


13C{1H}/ 13C{1H,19F} NMR (125 MHz, CD2Cl2, 298K): 186.8 (s, dioxolium),158.0 (s, dioxolium), 148.7 (m, 1JCF = 240 Hz), 148.2 (s, dioxolium), 139.0 (m, 1JCF ca. 234 Hz), 137.2 (m, 1JCF ca. 246 Hz), 124.1 (q, 1JCB = 50.0 Hz), 37.2 (s), 26.6 (s, 3C), 25.0 (s), 20.8 (s), 19.0 (q, 1JCB = 40.0 Hz), 13.6 (s).

EA (elemental analysis) calcd (%) for [C29H18O2BF15*0,5C7H8]: C 52.73; H 3.00; Found: C 52.60, H 3.09.

HRMS-DART (+) (m/z): calcd for [C29H18O2BF15+NH4]+, 712.1504; found, 712.14919.

2. NMR Spectra

1H NMR (400 MHz, CDCl3, 298K) spectrum of but-2-yn-1-yl 4-methylbenzoate (1)

1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

2.85

3.00

2.00

2.09

1.78

1.88

2.41

4.87

7.23

7.25

7.95

7.97

13C NMR (100 MHz, CDCl3, 298K) spectrum of but-2-yn-1-yl 4-methylbenzoate (1)

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

3.85

21.8

3

53.2

6

73.5

4

83.2

8

127.

1512

9.22

129.

95

143.

99

166.

23

1H NMR (400 MHz, CDCl3, 298K) spectrum of hex-2-yn-1-yl 4-methylbenzoate (2)

13C NMR (100 MHz, CDCl3, 298K) spectrum of hex-2-yn-1-yl 4-methylbenzoate (2)

1H NMR (400 MHz, CDCl3, 298K) spectrum of hex-2-yn-1-yl pivalate (3)

13C NMR (100 MHz, CDCl3, 298K) spectrum of hex-2-yn-1-yl pivalate (3)

1H NMR (500 MHz, CD2Cl2, 298K) spectrum of (4)

2.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

2.85

3.00

2.10

2.22

2.01

2.20

2.55

2.95

2.96

7.51

7.53

7.85

7.87

11B NMR (128 MHz, CD2Cl2, 298 K) spectrum of (4)

-50-40-30-20-100102030405060708090100110120130f1 (ppm)

-14.

33

19F NMR (377 MHz, CD2Cl2, 298 K) spectrum of (4)

-220-210-200-190-180-170-160-150-140-130-120-110-100-90-80-70-60-50-40-30f1 (ppm)

2.01

1.00

2.12

-166

.29

-166

.23

-166

.18

-161

.96

-161

.91

-161

.86

-132

.80

-132

.74

-132.9-132.7f1 (ppm)

2.12

-132

.80

-132

.74

-162.0-161.8f1 (ppm)

1.00

-161

.96

-161

.91

-161

.86

-166.4-166.0f1 (ppm)

2.01

-166

.29

-166

.23

-166

.18

13C NMR (125 MHz, CD2Cl2, 298K) spectrum of (4)

0102030405060708090100110120130140150160170180f1 (ppm)

9.00

18.5

718

.94

19.2

319

.51

23.0

7

113.

65

130.

9913

2.19

136.

3013

7.99

138.

0313

9.96

143.

5014

7.79

149.

6815

3.79

173.

02




13C NMR {1H} (125 MHz, CD2Cl2, 298K) spectrum of (5)

13C NMR {1H; 19F at -132 ppm} (125 MHz, CD2Cl2, 298K) spectrum of (5)


1H/13C-HMBC (500/125 MHz, CD2Cl2, 298K) spectrum of (5)




13C NMR {1H} (125 MHz, CD2Cl2, 298K) spectrum of (6)



1H/13C-HMBC (500/125 MHz, CD2Cl2, 298K) spectrum of (4)

In situ 11B NMR (96 MHz, CD2Cl2, 298K) spectrum at various time intervals.

IR spectrum (ATR) of (5)

IR spectrum (ATR) of (6)

3. DFT Studies

Computational Details

Gas phase geometry-optimised structures for 4 were determined using the B3LYP functional and 6-

31G* basis set within Jaguar.2 Additional DFT calculations were performed on the B3LYP/cc-pVDZ

level of theory with Gaussian093. Frequency calculations were performed on all structures and minima

on the potential energy surface and minima were uniquely characterized by zero imaginary

frequencies. NBO analyses4 were undertaken to probe the dominant Lewis structure for 4. NBO partial

charges (left) and bond orders (right) for 4 based on the DFT-optimised (B3LYP/6-31G*) geometry

are shown below:

The frontier orbitals of 4 are shown in Figure below.

HOMO LUMO

O

O

p-tol

Me

B(C6F5)3

+0.82

-0.43

+0.24

+0.33

-0.41O

O

p-tol

Me

B(C6F5)30.97

0.98

0.97

1.790.97

4. Crystallographic Details

X-ray diffraction studies to determine the solid-state structure of crystalline materials were undertaken

on single crystals grown under an inert atmosphere and protected from atmospheric air and moisture

using an inert per-fluorinated polyether oil. A single crystal was then mounted in a cryoloop. For

compound 4: Crystals were examined on a Bruker APEX-II diffractometer using monochromatic Mo-

Kα radiation (0.71073 Å) and a CCD area detector. Data were collected at 150(2) K with temperatures

maintained using an Oxford Cryostream cooler for both initial indexing and full data collection. Data

were processed using SAINT and an absorption correction applied using multi-scan within the APEX-

2 program.5 The structures were solved by direct methods within the SHELXTL package. All

structures were refined against F2 using the SHELXTL package.6 Crystal data for 4: C30H12BF15O2, M

= 700.21, triclinic P-1, a = 10.6886(5), b = 11.3024(5), c = 12.7940(6) Å, α = 67.050(2), β =

74.863(2), γ = 83.714(2)o, V = 1373.83(11) Å3 , λ(Mo-Kα) = 0.71, T = 150(2) K, Z = 2, Dc = 1.693

Mg m-3, F(000) = 696, independent reflections 7118 (Rint = 0.0887), R1 (I > 2σ(I)) = 0.0441, wR2 (all

data) = 0.1000, S = 1.007 (all data). For compound 5: Crystals were examined on a Bruker APEX-II

diffractometer using monochromatic Mo-Kα radiation (0.71073 Å) and a CCD area detector. Data

were collected at 200(2) K with temperatures maintained for full data collection. Crystal data for 5:

C32H16BF15O2,colourless crystal (plate), dimensions 0.280 x 0.200 x 0.080 mm3, crystal system

monoclinic, space group P21/c, a = 11.732(2) Å, b = 20.805(4) Å, c = 13.426(2) Å, α = 90°, β =

107.896(4)°, γ = 90°, V = 3118.5(9) Å3, T = 200(2) K, Z = 4, Dc = 1.642 Mg m-3, Thetamax= 24.108°,

λ(Mo-Kα) = 0.71073 Å, 0.5° omega-scans with CCD area detector, covering the asymmetric unit in

reciprocal space with a mean redundancy of 3.05 and a completeness of 100.0% to a resolution of

0.83Å, 16881 reflections measured, 4974 unique (R(int)=0.0397), 3703 observed (I > 2σ(I)),

intensities were corrected for Lorentz and polarization effects, an empirical absorption correction was

applied using SADABS7 based on the Laue symmetry of the reciprocal space, mu=0.25mm-1,

Tmin=0.90, Tmax=0.96, structure refined against F2 with a Full-matrix least-squares algorithm using the

SHELXL (Version 2013-4) software6, 479 parameters refined, hydrogen atoms were treated using

appropriate riding models, goodness of fit 1.03 for observed reflections, final residual values

R1(F)=0.040, wR(F2)=0.101 for observed reflections, residual electron density -0.53 to 0.57 eÅ-3.

Unit cell parameters and refinement statistics are presented in Table 1. For additional data see: CCDC

987406 and CCDC 987407.

Table 1: Selected Crystallographic Data for 4 and 5.

Compound 4Empirical Formula C30H12BF15O2 T /K 150(2)Crystal System Triclinic Dc/g.cm-3 1.693Space Group P-1 Crystal size/mm 0.10 0.10 0.10a/Å 10.6886(5) Total data 7118b/Å 11.3024(5) Unique data 4464c/Å 12.7940(6) Rint 0.0887/o 67.050(2) R1[F2>2 (F2)] 0.0441/o 74.863(2) wR2 (all data) 0.1000/o 83.714(2) GoF 1.007V/Å3 1373.83(11) min/max/eÅ-3 -0.282/+0.337Z 2

Compound 5Empirical Formula C32.50H17BClF15O2 T /K 200(2)Crystal System monoklin Dc/g.cm-3 1.64Space Group P21/c Crystal size/mm 0.28x0.20x0.08a/Å 11.732(2) Total data 16881b/Å 20.805(4) Unique data 4974c/Å 13.426(2) Rint 0.0397/o 90.0 R1[F2>2 (F2)] 0.040/o 107.896(4) wR2 (all data) 0.101/o 90.0 GoF 1.03V/Å3 3118.5(9) min/max/eÅ-3 -0.53/0.57Z 4

5. References:

1. H. -J. Frohn in “Efficient Preparations of Fluorine Compounds” (chapt. 10), 1. Ed., H. W.

Roesky (Ed.), Wiley-VCH, Weinheim, 2013.

2. Jaguar, version 7.7, Schrodinger, LLC, New York, NY, 2010.

3. Gaussian 09, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A.

Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji,

M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M.

Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O.

Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J.

Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K.

Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M.

Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts,

R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L.

Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S.

Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox,

Gaussian, Inc., Wallingford CT, 2010.

4. NBO 5.0. E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C.

M. Morales and F. Weinhold (Theoretical Chemistry Institute, University of Wisconsin,

Madison, WI, 2001); http://www.chem.wisc.edu/~nbo5

5. APEX2 and SAINT software; Bruker AXS Inc., Madison, Wisconsin, USA.

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7. Program SADABS 2012/1 for absorption correction; G.M. Sheldrick, Bruker Analytical X-

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Structural Characterisation of 1,3-Dioxolium Compounds 6 5 ...

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